Design, semisynthesis and insecticidal activity of novel podophyllotoxin derivatives against Brontispa longissima in vivo

In an attempt to find the effective phytopesticides, a series of novel podophyllotoxin derivatives were firstly synthesized and preliminarily tested for their antifeedant and insecticidal effects against the fifth-instar larvae of Brontispa longissima. The different antifeedant and insecticidal activity ranges of compounds 3a-l showed that variations of NR1R2 groups in the 4-position of podophyllotoxin skeleton markedly affected the activity profiles of this compound class, and some important SAR information has been revealed from it. To clarify their mode of action of insecticidal activity, the docking models as well as tubulin inhibitory effect of representative compound 3i were also investigated, and the result indicated that the insecticidal activity of these compounds was due to the tubulin inhibitory effect of these derivatives, thereby possibly providing some useful information for rational designs of novel podophyllotoxin-based insecticides.

A series of novel podophyllotoxin derivatives were firstly synthesized via a Cu-catalyzed one pot reaction for their insecticidal activity studies.Figure optionsDownload as PowerPoint slideHighlights
► Insecticidal activity of 4β-O-sulfonyl amidine podophyllotoxin derivative against Brontispa longissima was firstly reported.
► Their insecticidal activity results are encouraging and important SAR clues has revealed from it.
► Molecular docking and study of mechanisms contributed to a better development of podophyllotoxin-derived insecticides.